Diamond Head Oahu

Oahu Vacation Packages

 
Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cusine. Our selection of Waikiki hotels and resorts offer great locations near entertainment and iconic beaches. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture gives Oahu a flavor all its own.
 

Exclusive 5-day two-category car rental upgrade
From intermediate to convertible, Jeep, luxury or SUV

  • Minimum 5-night vacation packages
  • Book by 7/7/19 for travel through 12/14/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Aqua Ohia Waikiki
    Aqua Ohia Waikiki
    Waikiki, Oahu Our 2-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment.

    Situated in the heart of one of the world’s most popular vacation destinations, this hotel is close to shopping, restaurants, and nightlife.
    • Hotel Room
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $686+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
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  • Sheraton Princess Kaiulani
    Sheraton Princess Kaiulani
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

    • Princess Tower City Side
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $718+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
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  • Luana Waikiki Hotel & Suites
    Luana Waikiki Hotel & Suites
    Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This contemporary boutique hotel located just a short stroll to Waikiki Beach features beautifully furnished accommodations in a desirable location on Kalakaua Avenue.
    • City View
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $776+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
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  • Aston Waikiki Sunset
    Aston Waikiki Sunset
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Just two blocks to Waikiki Beach, this relaxed family oriented condominium resort features island style living with their one- and two-bedroom accommodations with full kitchens.
    • One Bedroom Standard
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $810+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
    See Details
  • Hilton Hawaiian Village Waikiki Beach Resort
    Hilton Hawaiian Village Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

    • Resort View King
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $928+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
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  • Hyatt Regency Waikiki Beach Resort and Spa
    Hyatt Regency Waikiki Beach Resort and Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Explore the excitement of Oahu in one of Hawaii’s most fashionable zip codes. Just steps from renowned warm waters and spectacular views.

    • Waikiki City View King
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • Reduced rates

    5 nights with flight from $998+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
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  • Waikiki Beachcomber by Outrigger
    Waikiki Beachcomber by Outrigger
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "An Oasis in the Heart of Waikiki" This brand new lifestyle resort which just completed a $35 million modernization offers contemporary comfort, camaraderie and fun.
    • Waikiki View King
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $1030+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
    See Details
  • Moana Surfrider, A Westin Resort & Spa
    Moana Surfrider, A Westin Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

    • Historic Banyan
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • 15% spa discount
    • Daily Beach Club access for up to two people per room

    5 nights with flight from $1094+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
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  • Outrigger Waikiki Beach Resort
    Outrigger Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    “Where the Beach Comes Alive” Our extended ohana (family) will discover local beach and surf culture at this hotel on Waikiki Beach.
    • Partial Ocean View King
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • Daily breakfast, brunch or lunch for two

    5 nights with flight from $1136+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
    See Details
  • Turtle Bay Resort
    Turtle Bay Resort
    North Shore, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Surrounded by the beauty and majesty of O'ahu's legendary North Shore, this luxurious resort embodies the very essence of Hawaii.

    • Ocean View King
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $1284+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
    See Details
  • The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This legendary hotel, known as the Pink Palace of the Pacific, offers a redefined luxury experience.
    • Historic
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • Daily breakfast buffet at Surf Lanai Restaurant for up to two people per room
    • 15% spa discount

    5 nights with flight and car from $1431+

    Los Angeles, California (LAX) departures, valid for travel 08/26/19
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  • Aulani, A Disney Resort & Spa
    Aulani, A Disney Resort & Spa
    Ko Olina Resort Area, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Inspired by the wonders and traditions of Hawaii, Aulani has been uniquely designed for families.

    • Standard
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV
    • Reduced rates

    5 nights with flight from $1574+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
    See Details
  • Aston Waikiki Beach Tower
    Aston Waikiki Beach Tower
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Recently renovated, this exclusive condominium resort offers spacious and elegantly furnished with one and two-bedroom suites with fully-equipped chef inspired kitchens, in-room washer/dryer and ocean views.
    • One Bedroom Ocean View
    • Receive a FREE two-category car rental upgrade from Midsize to Convertible, Jeep, Luxury or SUV

    5 nights with flight from $1972+

    San Jose, California (SJC) departures, valid for travel 08/26/19 - 08/31/19
    See Details
Hawaii - Two-Category Car Rental Upgrade Offer: Valid on new bookings made 6/3 - 7/7/19 for travel 6/3 - 12/14/19. Roundtrip airfare and minimum 5 nights' hotel accommodation at participating hotel required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV for five days.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]